The Matchmaker
by jdmusiclover
Summary: CS Modern AU. Mary Margaret Nolan knows Emma and Killian would be perfect for each other, so she takes it upon herself to make sure Killian gets Emma's name for the office Secret Santa exchange.


The Matchmaker

 _Today's story is an AU based on this prompt from kmomof4:_ _Character A's best friend rigs the Secret Santa, because they know Character A has a crush on Character B. This story can also be found as chapter 117 of my Fluffy Fridays collection and as the 4_ _th_ _day of my 20 days of Christmas collection on Tumblr._

 _ **Rating:**_ _K+_

 _Notes: I wanted this au to take place in an office setting—so I set it in Storybrooke's version of my own workplace, the library._

David closed his eyes and was just beginning to doze off when his wife, Mary Margaret shook his shoulder gently. "You awake?"

David chuckled and rolled to his side to face the love of his life. "I am now."

"Good," Mary Margaret said, and David could nearly hear the excitement radiating off of her in waves, "because I just had the best idea _ever_!"

"Well this I have to hear."

"You know the new guy in serials cataloging? Killian?"

"I would hope I know him," David said with another chuckle. "I am his supervisor after all."

David noted his wife's broad smile by the light of the full moon shining into their bedroom. "You know who would be _perfect_ for him?"

David groaned. "Mary Margaret, I thought you decided you were done with matchmaking after the disaster that was your last attempt."

Mary Margaret huffed. "Okay, I admit that Nottingham wasn't exactly Ruby's perfect match…or anyone's perfect match. But everyone can have an off day, right?"

"And after that fiasco, your best friend refused to speak to you for a week."

"Ruby knows I have the best of intentions," Mary Margaret said, "and she did forgive me for the Nottingham miscalculation…eventually. Anyway, never mind that, now. My newest matchmaking venture is _perfect_."

David sighed in good natured exasperation. "Alright then, let's have it. Who's _perfect_ for Killian?"

"Emma, of course!" Mary Margaret said. "You know, she's practically family, and I feel it my duty to help my family find perfect happiness."

"Mary Margaret, you do realize, don't you, that Emma's spent the better part of every day since Killian's arrival sighing in exasperation at him? When I asked her to train him to be her backup on collections statistics, I thought her look would kill me."

Mary Margaret waved away his objection. "You poor, clueless man! Don't you realize she's reacting like that because she _does_ have feelings for him? Feelings she doesn't want to have, of course, but feelings still. She's just afraid to take a chance that her gut feeling is wrong about him."

David eyed her skeptically. "I don't know about that…"

"Well, I do," Mary Margaret said, "and anyone with eyes can see that he's already head over heels in love with her."

"I'm sure I'm going to regret asking this," David said, "but what nefarious matchmaking scheme do you have in mind this time?"

"You know the office Christmas party is coming up," Mary Margaret said, "and as unit secretary, it's my job to organize the Secret Santa. If Killian just _happened_ to get Emma's name…well, you never know what might come of it."

"Let's just hope what comes of it isn't bloodshed," David muttered.

"Just you wait, David Nolan," Mary Margaret answered confidently. "This time next year we'll be getting a wedding invite from those two."

~c~s~c~s~c~s~c~s~c~s~

Killian rummaged around in the festive Santa hat Mary Margaret was holding out to him. Finally, deciding on the slip of paper he wanted, he withdrew his hand and looked at the name of his Secret Santa giftee.

 _Emma Swan_

Killian's stomach swooped pleasantly, and his heart started racing. _Emma_. The woman whose desk was next to his. The most beautiful woman he'd ever seen. The strongest, bravest, most fascinating woman in the world. The woman he fell in love with nearly the instant he'd laid eyes on her.

The woman who seemed to despise him with everything within her.

Killian folded the slip of paper and handed it back to the secretary. Mary Margaret glanced at the name he'd received, noted it on her masterlist of Santas and giftees, and then grinned at him. "This is your opportunity Killian," she said so softly that no one else could hear.

"Beg pardon? My opportunity for what?"

"Your opportunity to show Emma just how much you care for her."

Killian felt his face color as he reached up to scratch at the spot behind his ear. "I don't…"

"Oh don't even try to deny it," she said with a knowing smile. "I'm married to my true love, remember? David and I are practically Snow White and Prince Charming. I _know_ love when I see it, and you, Killian Jones have it _bad_ for Emma Swan."

Killian chuckled nervously. "I won't deny that I rather fancy her when she's not yelling at me. But therein lies the rub. She's almost _always_ yelling at me. Hardly the behavior of a woman who wishes to be wooed."

"That's where you're wrong," Mary Margaret said. "I've known Emma ever since we met in kindergarten. The thought of being vulnerable, of opening herself up to someone, of letting herself care _terrifies_ her. The more strongly she feels toward someone, the higher the wall she builds around her heart."

Killian sighed. "If that's true, she must be desperately, devastatingly in love with me."

"Now you're getting it!"

"I don't wish to contradict a lady," Killian pressed, "but I've flirted with the lovely Lady Swan from dawn to dusk for the past month, and there hasn't been so much as a crack in that wall."

Mary Margaret shrugged. "So prove to her you're not just a hot, ladies man who'd flirt with anything breathing. Use this opportunity to show her how much you truly care."

 _Show her how much you truly care_. The idea had merit, Killian couldn't deny it. Perhaps Mary Margaret was right. Perhaps this was his opportunity to win Swan's heart.

~c~s~c~s~c~s~c~s~c~s~

Emma arrived at her desk bright and early the next morning to find a steaming mug of cocoa topped with her favorite—whipped cream and cinnamon. She inhaled deeply, smiling at the comforting, slightly spicy chocolate scent. Picking up the note set beside the mug, she read.

 _Merry Christmas, Emma! The elves prepared a special Yuletide brew just for you. Have a lovely day. ~Santa~_

Emma brought the mug to her lips, took a sip, and then groaned in ecstasy. This wasn't just hot cocoa. This was the nectar of the gods. Whoever her secret Santa was, he or she knew how to make a _good_ cup of cocoa.

A deep masculine chuckle came from the desk next to her, and Emma felt her heart pick up its pace. That knowing, somehow innuendo-laden sound did obscene things to her insides.

Which was why, of course, she had to turn a furious scowl upon the man who'd made the sound. Killian Jones was a flirt, a ladies man, someone who had 'mistake' written all over him.

"It looks as though someone is enjoying their gift from Santa."

"Well I was," Emma muttered. "Before someone decided to open his big mouth."

"I shall endeavor to let you enjoy your beverage in peace," Killian said with a grin. "Your Santa seems to have hit upon the perfect gift."

"Whoever Santa is, they _get_ me," Emma agreed.

"One can only dream," Killian muttered under his breath.

Emma ignored the enigmatic statement from her annoying desk mate.

Over the course of the month, Emma continued to receive little gift after little gift from her Santa. A swan Christmas ornament. A grilled cheese sandwich for lunch, little baubles for her car. Fingerless gloves (that came the day after Emma had complained about the library keeping the office roughly the temperature of a meat locker), a CD of Christmas music, a big, sticky bear claw.

Emma actually found herself getting excited about coming into work each day, the anticipation of Santa's newest offering bringing a smile to her face as she prepared for the day.

It wasn't the stuff that touched her the most, it was the fact that her Santa seemed to truly know herher. He or she seemed to read her like an open book, always choosing just what she wished for at any given time.

She had a feeling that whoever this Santa was, she was going to walk away from the Christmas party on the last day before break with a new friend.

~c~s~c~s~c~s~c~s~c~s~

Killian took a deep breath to steady his nerves as the big Secret Santa reveal approached at the annual cataloging department Christmas party. This was the moment, the opportunity for him to put all his cards on the table. He knew he was taking a risk with the gift he'd selected for Swan, but with every passing day she became dearer to him, and he must, he simply _must_ take the chance on her.

"Alright," Mary Margaret said with a special twinkle in her eyes. "Emma, you're up. That small, rectangle gift is from your Santa.

Killian watched as the gentle smile spread over Emma's features. He hoped and prayed that expression would remain even after she learned his identity. Pulling the decorative paper free from the box, Emma opened it to reveal the delicate swan pendant on a silver chain that he'd had specifically commissioned for her. The smile on her face blossomed yet farther.

"It's gorgeous!" she breathed. "Alright, I've been dying to ask all month. Santa, who are you?"

Killian took one more deep breath and then stepped forward. "That would be me."

~c~s~c~s~c~s~c~s~c~s~

Emma went back to her desk later that afternoon in a daze. _Killian_. Killian was her secret Santa? Killian was the one who'd given her all those perfect, thoughtful gifts all month long? Was it possible? Was there more to her drop dead gorgeous desk mate than met the eye? Had she misjudged him all along?

"Hey," she said, swiveling her chair in Killian's direction.

"Aye, love?"

"Thanks," she said simply, reaching up to touch the necklace he'd given her. "Not just for this, but for, you know, all you've done all month. It's…it's meant a lot."

"I'm pleased you enjoyed it, Swan," he said, his voice almost shy.

"How did you do it?" she asked. "How did you always know _exactly_ what to get me, exactly what I craved?"

He scratched at the spot behind his ear, refusing to meet her eyes. "I pay attention. You may not believe it, but your heart's desire. That's all I've ever wanted from you."

Emma felt her stomach swoop and the tears come to her eyes. She could tell when someone was lying, had always had that 'super power', and this man was most definitely _not_ lying. He cared about her, really, truly cared about her.

Before she could think better of it, Emma leaned over and kissed him softly, gently. When she pulled back she noted his eyes still closed, a soft, almost reverent "Emma" falling from his lips, before he seemed to pull himself together.

"Well if that's the reaction I'm to get for my troubles," he said in a lame attempt to fall back on his old innuendo, "I shall have to shower you with gifts more often."

"I think I misjudged you," she said in return, "and I'm glad.

"As am I."

They sat in silence for another moment, before Killian reached into his pocket and pulled out a slip of paper. "I have one more gift for you, Swan."

Emma took the proffered offering, looking down to see the details of a reservation for two that night at the upscale Italian restaurant on the other side of town. "I thought, perhaps you might enjoy a night out as the madness of the holidays ramps up."

Emma smiled, feeling the tears threaten once more. "I'll accept them, on one condition."

"Aye, what's that?"

"I'll accept them if you'll be my date for the night."

Killian's smile could light up the darkest day of the year. "I'll pick you up at 7."

~c~s~c~s~c~s~c~s~c~s~

One year, almost to the day, later, Mary Margaret Nolan rummaged through the mail as she and David made their way upstairs to their loft apartment. When her eyes landed on an envelope with fancy script, she squealed in delight. Opening the offering, she perused its contents.

 _Emma Swan and Killian Jones request the honor of your presence at their wedding on the seventeenth day of June two thousand eighteen._

David grinned, shaking his head good-naturedly. "There'll be no living with you after this, will there?"


End file.
